Potassium Carbonate → HCID 54200145, compound

HRID 2309045Notes

Reaction equation

HRID 2309045 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Br[CH:10]([C:14]([F:17])([F:16])[F:15])[C:11](Cl)=[O:12].[S:18]1C=C[CH:20]=[C:19]1CC(O)=O.C(=O)([O-])[O-].[K+].[K+].[OH-:33].[Na+]>O>[C:19]([S:18][CH:10]([C:14]([F:17])([F:16])[F:15])[C:11]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:12])(=[O:33])[CH3:20]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 159702-Thiopheneacetic acidHCID 145742L-ProlineHCID 540458592-Bromo-3,3,3-trifluoropropanoyl chloride

Product 1

HCID 54200145HCID 54200145, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of L-proline (5.75 g.) in 1N sodium hydroxide (50 ml.), chilled in an ice-water bath, 2-bromo-3,3,3-trifluoropropanoic acid chloride (12 g.) is added and the mixture is vigorously stirred at room temperature for three hours. A solution of thiolacetic acid (4 ml.) and potassium carbonate (4.8 g.) in water (50 ml.) is added and the mixture is stirred at room temperature for sixteen hours. After extraction with ethyl acetate, the aqueous layer is acidified with concentrated hydrochloric acid and extracted again with ethyl acetate. This last organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo. The residue is chromatographed on a silica gel column with a mixture of benzene-acetic acid (7:2) to yield N-(2-acetylthio-3,3,3-trifluoropropanoyl)-L-proline. The named product is obtained by following the procedure of Example 33.

Workup

  1. stirringthe mixture is stirred at room temperature for sixteen hours
  2. extractionAfter extraction with ethyl acetate
  3. extractionextracted again with ethyl acetate
  4. dry with materialThis last organic phase is dried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue is chromatographed on a silica gel column with a mixture of benzene-acetic acid (7:2)

Sources & evidence

ORD record
ord-1d31d63abc2f4e80ad78bd28c84151da
Source dataset
uspto-grants-1987_09
Patent number
US04692458

Reaction notes

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